Bart dumps Milhouse in favor of a cute girl who volunteers her time at the retirement home; and Lisa is prescribed antidepressants after she reads predictions about what Springfield will look like in 50 years.

Bart and Milhouse use power screwdrivers to stage a prank at Springfield Elementary. Before long, anything held together with a screw falls apart. Principal Skinner grabs Bart and Milhouse by the back of their pants, and leads them away. Even Chalmers falls victim to the prank: he ends up with a toilet stuck on his head. A short time later, Skinner and Chalmers tell Milhouse that half of a blue eyebrow implicates him in the mischievous prank. Milhouse refuses to name his accomplice, so he’s suspended from school for a week. Bart thanks Milhouse for his loyalty, and promises to visit him during his suspension. Later, Homer drives Bart to the retirement home. Homer instructs Bart to visit Grampa... and to use Homer’s name when he signs in. That way, the next day Grampa will think Homer paid him a visit. When Bart enters the retirement home, he’s surprised to discover the elderly residents playing a Nintendo Wii-like game. It turns out that an eleven-year-old girl named Jenny Cleary taught the old-timers how to play video games. Bart is instantly smitten with Jenny. Hoping to impress her, he pretends to enjoy spending time with the retirees. He even gives Grampa a hug. Meanwhile, Lisa works on a social studies project for school. Using the Internet, she researches information about what Springfield will be like in 50 years. When she reads predictions about the world becoming a drought-ridden place where Jenna Bush is president, she grows depressed. At school, Nelson urges Bart to claim Jenny as his own by punching her in the arm; however, Bart thinks better of it. Instead Bart asks Jenny out on a date, and she accepts.

When Lisa delivers her report on what Springfield will be like in fifty years, she warns of gloom and doom. Meanwhile, Bart and Jenny picnic in a peaceful glade. Jenny asks Bart how he intends to make the world a better place. Thinking quickly, Bart points out Homer, and says he works with the mentally challenged. Later Bart and Jenny go for a ride in a rowboat. During the trip Jenny reacts with shock when she sees bullies Jimbo, Dolph, and Kearney teasing a mother duck by playing “keep-away” with one of her offspring. Jenny pleads with Bart to do something, so Bart jumps into the water and swims toward the bullies. Bart quietly pleads with the threesome to stop what they’re doing, and explains that he’s trying to impress a girl. It turns out the bullies are trying to impress a girl as well. The bullies release the duckling... and beat up Bart in exchange for their cooperation. Marge grows concerned about Lisa’s behavior. She brings Lisa to a psychiatrist, who asks her a series of questions. Eventually Lisa is diagnosed with Environment Related Despair. Luckily a new drug called Ignorital cures the illness. Lisa decides that the only way to get through life is to be self-medicated and numb. Lisa starts taking her medication, which makes her view the world as a happy place filled with happy faces. Bart and Jenny’s relationship intensifies. Jenny kisses Bart at an ice-cream parlor, causing his ice cream to melt. Bart even offers to do chores around the house, hoping Marge will put in a good word for him when Jenny comes to dinner. The dinner goes off without a hitch… until a disgruntled Milhouse shows up at the front door. As lightning flashes and thunder rumbles, Milhouse wants to know why Bart never visited him during his suspension from school.

Bart tells Milhouse that he’s kept his dark past a secret from Jenny. Milhouse tells Bart he won’t stand in the way. Jenny asks Bart if there’s anything she should know about him. Bart decides to keep quiet. During church service, Jenny suggests that Milhouse accompany her and Bart on their trip to juice country. Bart continues to push Milhouse away. Homer swallows a bunch of Lisa’s pills. Before long he mistakes his hands for ice-cream cones, and sucks on them until they bleed. Lisa, however, begins to come out of her stupor when she sees a squirrel struggling to climb out of a garbage can. She decides not to take any more pills. Milhouse continues to act creepy around Bart and Jenny. Eventually Bart tells Jenny that he has a dark past. Jenny responds by dumping him.

A despondent Bart makes his way to the Kwik-E-Mart, where he downs Squishee after Squishee. Lisa urges Bart not to wallow in despair. She urges him to take action and set things straight. Bart realizes Lisa is right. He buys some roses... and brings them to Milhouse. Milhouse forgives Bart for the way he’s been acting. Later Bart and Milhouse ice over the floors of Springfield Elementary with some help from a Zamboni, and Milhouse uses asbestos to make it seem like it’s snowing.